Site specific 1:1 opioid:albumin conjugate with in vitro activity and long in vivo duration

Bioconjugate Chemistry

Volumn 11, Issue 4, 2000, Pages 439-444

  Holmes, Darren L ^a   Thibaudeau, Karen ^a   L'Archevêque, Benoît ^a   Milner, Peter G ^a   Ezrin, Alan M ^a   Bridon, Dominique P ^a  

^a INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINOCICEPTIVE; HUMAN SERUM ALBUMINS; IN-VITRO; IN-VIVO; LONG LASTING; OPIOID RECEPTORS; OPIOIDS; SITE-SPECIFIC; VITRO ACTIVITY; WRITHINGS;

MAMMALS;

ANIMALIA; CRICETINAE;

EID: 0033891283     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0000233     Document Type: Article

References (37)

1. Cox, B. M., Opheim, K. E., Teschenmacher, H., and Goldstein, A. (1975) A peptide-like substance from pituitary that acts like morphine. 2. Purification and properties. Life Sci. 16, 1777-1782.
2. Goldstein, A., Tachibana, S., Lowney, L. I., Hunkapiller, M., and Hood, L. (1979) Dynorphin-(1-13), an extraordinarily potent opioid peptide. Proc. Natl. Acad. Sci. U.S.A. 76, 6666-6670.
3. Goldstein, A., Fischli, W., Lowney, L. I., Hunkapiller, M., and Hood, L. (1981) Porcine pituitary dynorphin: Complete amino acid sequence of the biologically active heptadecapeptide. Proc. Natl. Acad. Sci. U.S.A. 78, 7219-7223.
4. Naqvi, T., Haq, W., and Mathur, K. B. (1998) Structure-activity relationship studies of dynorphin A and related peptides. Peptides 19, 1277-1292.
5. 1 Conformational Constraint in the "Address" Sequence. J. Med. Chem. 40, 1211-1218.
6. Chavkin, C., James, I. F., and Goldstein, A. (1982) Dynorphin Is a specific endogenous ligand of the κ opioid receptor. Science 215, 413-415.
7. James, I. F., and Goldstein, A. (1984) Site-directed alkylation of multiple opioid receptors. I. Binding selectivity. Mol. Pharmacol. 25, 337-342.
8. Garzon, J. G., Sanchez-Blazquez, P., Gerhart, J., Loh, H. H., and Lee, N. M. (1984) Dynorphin 1-13: interaction with other opioid ligand bindings in vitro. Brain Res. 302, 392-396.
9. Snyder, K. R., Story, S. C., Heidt, M. E., Murray, T. F., DeLander, G. E., and Aldrich, J. V. (1992) Effect of Modification of the Basic Residues of Dynorphin A-(1-13) Amide on κ Opioid Receptor Selectivity and Opioid Activity. J. Med. Chem. 35, 4330-4333.
10. Smith, A. P., and Lee, N. M. (1988) Pharmacology of Dynorphin. Annu. Rev. Pharmacol. Toxicol. 28, 123-140.
11. Kreek, M. J., Schluger, J., Borg, L., Gunduz, M., and Ho, A. (1999) Dynorphin A1-13 causes elevation of serum levels of prolactin through an opioid receptor mechanism in humans: gender differences and implications for modulation of dopaminergic tone in the treatment of addictions. J. Pharmacol. Exp. Ther. 288, 260-269.
12. Gambús, P. L., Schnider, T. W., Minto, C. F., Youngs, E. J., Billard, V., Brose, W. G., Hochhaus, G., and Shafer, S. L. (1998) Pharmacokinetics of intravenous dynorphin A(1-13) in opioid-naive and opioid-treated human volunteers. Clin. Pharmacol. Ther. 64, 27-38.
13. Greenwald, M. K., Stitzer, M. L., and Haberny, K. A. (1997) Human pharmacology of the opioid neuropeptide dynorphin A(1-13). J. Pharmacol. Exp. Ther. 281, 1154-1163.
14. Uneklabh, T., Sintavanarong, P., Wessagowit, V., and Lukanapichonchut, L. (1995) Clinical effect of dynorphin on heroin addicts. J. Med. Assoc. Thai. 78, 509-16.
15. Giuffra, M., Mouradian, M. M., Davis, T. L., Ownby, J., and Chase, T. N. (1993) Dynorphin agonist therapy of Parkinson's disease. Clin. Neuropharmacol. 16, 444-447.
16. Muller, S., and Hochhaus, G. (1995) Metabolism of Dynorphin A 1-13 in human blood and plasma. Pharm. Res. 12, 1165-1170.
17. Muller, S., Dunker, R., and Hochhaus, G. (1996) Interspecies comparison of in vitro plasma degradation of dynorphin A 1-13. Pharmazie 51, 581-585.
18. Muller, S., Grundy, B. L., and Hochhaus, G. (1996) Metabolism of Dynorphin A1-13 in Human CSF. Neurochem. Res. 21, 1213-1219.
19. Muller, S., Ho, B., Gambus, P., Millard, W., and Hochhaus, G. (1997) An HPLC/RIA method for dynorphin A1-13 and its main metabolites in human blood. J. Pharm. Biomed. Anal. 16, 101-109.
20. Pentel, P. R., Wananukul, W., Hooke, L. P., Jones, C. R. N., Hatsukami, D., Anderson, W. R., and Lee, N. M. (1995) Effects of high intravenous doses of dynorphin A(1-13) on tail flick latency and central nervous system histology in rats. Pharmacol. Biochem. Behav. 51, 387-390.
21. Yaksh, T. L., and Noueihed, R. (1985) The physiology and pharmacology of spinal opiates. Annu. Rev. Pharmacol. Toxicol. 25, 433-462.
22. Banks, W. A. and Broadwell, R. D. (1994) Blood to Brain and Brain to Blood Passage of Native Horseradish Peroxidase, Wheat Germ Agglutinin, and Albumin: Pharmacokinetic and Morphological Assessments. J. Neurochem. 62, 2404-2419.
23. Peters, T. (1996) Metabolism: Albumin in the Body. In All about albumin: biochemistry, genetics, and medical applications (T. Peters, Ed.) pp 188-250, Academic Press, Inc., San Diego.
24. Allen, D. T., and Kiernan, J. A. (1994) Permeation of Proteins from the Blood into Peripheral Nerves and Ganglia. Neuroscience 59, 755-764.
25. Ezrin, A. M., Bridon, D. P., Holmes, D. L., and Milner, P. (1999) Novel Conjugates of Opioids and Endogenous Carriers, PCT, W09924074.
26. Dixon, F. J., Maurer, P. H., and Deichmiller, M. P. (1953) Half-Lives of Homologous Serum Albumins in Several Species. Proc. Soc. Exp. Biol. Med. 83, 287-288.
27. Hermanson, G. T. Bioconjugate Techniques, Academic Press, San Diego, 1996.
28. 32P-Labeled Opioid Peptides with High Affinity for the δ-Opioid Receptor. Anal. Biochem. 215, 1-8.
29. Peters, T. (1996) Tertiary Structure and Physical Chemical Behavior. In All about albumin: biochemistry, genetics, and medical applications (T. Peters, Ed.) pp 24-54, Academic Press, Inc., San Diego.
30. Park, K. B., Tingle, M. D., Grabowski, P. S., Coleman, J. W., and Kitteringham, N. R. (1987) Drug-protein conjugates - XI. Disposition and immunogenicity of dinitrofluorobenzene, a model compound for the investigations of drugs as haptens. Biochem. Pharmacol. 36, 591-599.
31. Wu, C. W., and Yarbrough, L. R. (1976) N-(1-pyrene)-maleimide: a fluorescent cross-linking reagent. Biochemistry 15, 2863-2868.
32. Hayashi, T., Shimoyama, Y., Kuwata, K., and Era, S. (1999) Investigation of slow dynamics of the sulfhydryl in the solution and gel states of bovine serum albumin: A vector electron paramagnetic resonance study. Jpn. J. Physiol. 49, 27-33.
33. Yasuzawa, T., and Tomer, K. B. (1997) Structural determination of the conjugate of human serum albumin with a mitomycin C derivative, KW-2149, by matrix-assisted laser desorption/ionization mass spectrometry. Bioconjugate Chem. 8, 391-399.
34. Maguire, P., Tsai, N., Kamal, J., Cometta-Morini, C., Upton, C., and Loew, G. (1992) Pharmacological profiles of fentanyl analogues at μ, δ and κ opiate receptors. Eur. J. Pharmacol. 213, 219-225.
35. Simonin, F., Gavériaux-Ruff, C., Befort, K., Matthes, H., Lannes, B., Micheletti, G., Mattéi, M.-G., Charron, G., Bloch, B., and Kieffer, B. (1995) κ-Opioid receptor in humans: cDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central nervous system. Proc. Natl. Acad. Sci. U.S.A. 92, 7006-7010.
36. Wang, J.-B., Johnson, P. S., Persico, A. M., Hawkins, A. L., Griffin, C. A., and Uhl, G. R. (1994) Human μ opiate receptor-cDNA and genomic clones, pharmacologie characterization and chromosomal assignment. FEBS Lett. 338, 217-222.
37. Hooke, L. P., He, L., and Lee, N. M. (1995) [Des-Tyr1]-dynorphin A-(2-17) has naloxone-insensitive antinociceptive effect in the writhing assay. J. Pharmacol. Exp. Ther. 273, 802-807.